Nitratoalkyl amides



Patented June 22, 1948 NITRATOALKYL AMIDES William Frederick Filbert, Woodbury, N. J., as-

signor to E. I. du Pont de Nemours & Company, Wilmington, Del., a corporation of Delaware No Drawing. Application December 30, 1941, Serial No. 424,993

2 Claims.

This invention relates to new explosive compounds comprising nitration products of hydroxy amides.

A great many materials and compounds have been proposed for use as explosive charges in detonators or blasting caps. Such compounds may function as base charges, primary charges, or ignition materials. While satisfactory results have been obtained in many respects with the compositions of the prior art, no material or combination of materials has been altogether free from disadvantages.

The object of the present invention is a new explosive compound, which is also a new composition of matter. Additional objects will be disclosed as the invention is described more at length hereinafter.

I have found that the foregoing object is at-- tained by treating with nitric acid, an amide of a hydroxy aliphatic monocarboxylic acid, to form a nitrated amide of said acid. In this nitration treatment, the addition of nitrogen results principally from the formation of nitric acid esters. In some cases nitro groups also are introduced. As examples of the resulting compounds, I may cite the preparation of N-nitro-N-methyl hydroxyacetamide nitrate from N-methyl hydroxyacetamide [CH2(ONO2)CON(NO2) -CI-Ial from [CH2(OH) -CO-NI-I-CH:] N-ethanol hydroxyacetamide dinitrate from N-ethanol hydroxyacetamide [CH2(ONO2)CONH-CHz-CHz-ONOz] from [CH2(OH) CONI-I-CH2-CHz-OH]; N-methyl gluconamide pentanitrate from N-methyl gluconamide [CH2(ONO2) (CHONOz) 4-CONH-CH3] from [CH2(OH) (CHOH) 4-CONH-CI'L3] N-ethanol gluconamide hexanitrate from N-ethanol gluconamide [CHzONOz (CHONO2) 4- CONH- CHz-CHzONOz] from [CI-IzOH(CI-IOH) 4-C0NI-I-CH2-CHzOHl gluconamide pentanitrate from gluconamide [CONI-Iz- (GHQ-N02) 4-CHZ2ONO2] from The following specific embodiments will serve to illustrate methods of preparing the compounds of my invention.

Example I Fifty grams of N-methyl hydroxy acetamide was added gradually to 150' cc. of 98.5% HNOa at a temperature below C. Stirring was continued while 150 g. of 96% sulfuric acid was added gradually at such a rate that the temperature did not exceed 5 C. The nitration mixture was then warmed. At 50 C. an active evolution of gas took place. The mixture was cooled and 2 poured into ice water. The creamy white solid separated in the form of small flat rectangular prisms. These were washed with water and purified by gradual dilution of their acetone solution. The material had a melting point of 79-81 C. and showed a nitrogen content of 15.52% when this latter was determined on the nitrometer as against a calculated value for such nitrogen of 15.63% for N-nitro-N-methyl hydroxy acetamide nitrate.

Example 2 Fifty grams of N-methyl gluconamide was added gradually to 200 cc. of 98.5% HNO; with vigorous stirring, keeping the temperature oi the mixture below 0 C. 200 cc. of acetic anhydride was added gradually, keeping the temperature below 5 C. 350 g. of cracked ice was then introduced with vigorous agitation. The solid material was separated, washed with water, cold dilute sodium bicarbonate solution, and again with water, and was t en dried at about 50 C. A yield was obtained of approximately 84% of theoretical, the material showing a nitrate-nitrogen content of 15.81% against a calculated value of 16.12% for N-methyl gluconamide pentanitrate. Recrystallization from hot methanol raised the nitrogen content to 15.90%.

Example 3 Thirty grams of gluconamide was added to 10 cc. of 98.5% HNOs, keeping the temperature below 0 C. cc. of technical acetic anhydride was then introduced with similar maintenance of low temperature. The mixture was diluted with ice and water and the white solid was washed-successively with water, sodium bicarbonate solution, and water. The dry material showed a nitratenitrogen content of 15.83%, which indicated that complete nitration to the pentanitrate had not taken place.

The new chemical compounds described in the foregoing possess attractive properties adapting them for use as explosive compounds, particularly as blasting cap charges. By reason of the introduction into the molecule of the nitrate groups, the compounds possess relatively high strength in addition to the sensitiveness necessary for their efiicient use. I find the compound resulting from the nitration of N-methyl gluconamide to be particularly effective for use as an explosive charge in blasting caps. It constitutes a desirable primer charge and may be employed as base charge also, if desired. Likewise it is an effective graining material for use with certain explosive compounds in finely divided form, diazo dinitrophenol for example, in order to promote free flowing characteristics. The blasting cap structure is not claimed herein, but is covered in copending application, Serial No. 426,319, filed January 10, 1942, U. S. Patent 2,420,306.

My invention .has been described .at length ,in the foregoing. "It will be understood, however, that other compounds not mentioned herein are intended to be included within the scope of the invention. I intend to be limited, therefore, only by the following patent claims.

I claim:

1. A a new compound, N-methylgluoonamide pentam'trate.

2. An amide having the following general formula wherein R is a nitrate lower alkyl, and R1 is a member of the group consisting of hydrogen, lower alkyl radicals and nitrato lower alkyl radicals.

WILLIAM FREDERICK FILBERT.

REFERENCES CITED The ,foilowing references-Lane of record in the file of this patent:

I-Iirwe: Chem. Abstracts. vol. 34, pp. 7882- 

